


How Pretty?

by RandomAlias1556



Category: Overwatch (Video Game)
Genre: Anal Fingering, Anal Sex, Blackwatch Era, Blackwatch Jesse McCree, Blackwatch Reaper | Gabriel Reyes, Blow Jobs, Crossdressing, Daddy Kink, Jesse is a beautiful boy and I will fight you on it, Light Dom/sub, Lingerie, M/M, Panties
Language: English
Status: Completed
Published: 2019-07-04
Updated: 2019-07-04
Packaged: 2020-06-03 19:22:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,907
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19470499
Author URL: https://archiveofourown.org/users/RandomAlias1556/pseuds/RandomAlias1556
Summary: Jesse has a habit of attempting to spice up the bedroom, whether Gabriel feels they need to or not. Jesse decides to try out a bit of cross-dressing this time around and Gabriel has no complaints.





	How Pretty?

**Author's Note:**

> This literally only occurred because I had an conversation with someone over how men can look amazing in tights and panties. The first character to pop into my head was Jesse McCree and suddenly this fic was born.

Being with Jesse McCree was a series of misadventures, as Gabriel had expected. At least he thought he expected it. The kid always found a way to surprise him some way or another. Normally that was with just how stupid he could be, but on occasion it was pleasant. Hell, sometimes it was even pleasurable. In fact, it was usually Jesse who decided he wanted to try something new.

It wasn’t that their sex-life needed spicing up, but Jesse was an experimental sort and always loved to switch things up a bit. Something about keeping it exciting. Gabriel didn’t think he’d ever stop being excited about sleeping with Jesse McCree. Sure, he was a pain in the ass most days at best, but he was loyal and caring and never missed a chance to shower Gabriel in affections. Affections that, with his track record, Gabriel rarely saw himself as deserving of. 

Gabriel was quick to let all of his doubts fall to the wayside when they were in such a scenario as they were now. He’s not sure where Jesse got the getup, but he certainly wasn’t complaining. Jesse was resting on the bed in Gabe’s private quarters, thin, black thigh highs nearly reaching the set of red panties he had decided on. To top it off he had on eyeliner, mascara, and bright red lipstick that were so well done that he imagined Jesse had to have had help, which, if he thought about it too much, would have embarrassed him greatly. Problem was, he currently was having immense trouble thinking passed the thoughts of what to do with the recruit. 

“You got all prettied up just for me, baby?” He practically purred as he crept closer, running a hand through his hair and ever so gently pulling. He took notice to the way Jesse’s eyes fluttered at the motion. 

“Sure did, papi,” The boy’s voice was blissed out already as if he was already falling into a headspace. 

“Be a shame to ruin all your work,” Gabriel teased, running a thumb just under his bottom lip to avoid smearing his lipstick. Jesse shuddered, a move that, had Gabe not learned every inch of him, would’ve gone unnoticed. 

“’s the point,” Jesse chuckled lightly, blinking his eyes back open as if he was still getting use to the amount of makeup surrounding them.

His eyes locked on Gabe’s and he wasn’t purely submissive anymore. He has that disobedient glint to his eyes that Gabe admired. No matter what you could never kill that fight in him, and Gabe never wanted to. Something about it was so ‘Jesse’ that if he ever did manage to erase it, he’s not sure he’d recognize his lover anymore.

“That so? You want me to rip these stockings off you? Want me to smear your makeup while I fuck your face?” Gabe growled, stalking forward like a predator with prey and placing a finger under the top of the socks. Jesse shivered under the attention and let out a rather shaky sigh. 

“Yessir,” he spoke loud and clear, eyes only leaving Gabe’s to glance at the hand that was skirting dangerously on the exposed skin between his panties and his stockings. As Jesse shifted under the predatory gaze of his lover, his muscle flexed and you could see them ripple from under the thin black fabric. 

“Then who would I be to deny you that? Since you went through all the trouble,” Gabe’s hungry glance was accompanied by a wolfish smile as he dug his fingers into the fabric of his stockings and tore them. There wasn’t a point to it, really. He could just slip them off, but he knew just how much Jesse loved shows of strength. The boy reacting beautifully with a surprised yelp that fell into a low, quiet moan. 

The tattered stockings were tossed aside and Jesse’s legs fell open invitingly. As much as Gabe wanted to take him right here and now, he had plans for him. He gave his boys thighs a squeeze and then lightly smacked his hip, earning another small noise of surprise.

“Up. Lay back on the bed for me,” Gabe commanded, his tone leaving no room for questions. With as much grace as the cowboy could muster, which wasn’t very much, he moved back to lay on the pillows, sprawling out and putting himself on display. Much to Gabe’s surprise, he held his hands above his head in a submissive gesture. He was being awfully good tonight and Gabriel was nearly overtaken with the desire to reward him handsomely for it. 

“You’re being so good for me, baby,” he acknowledged aloud, petting his thighs appreciatively and letting his eyes trail over his lover’s body. The boy shuddered and sighed happily at the praise, surprisingly, again, keeping his mouth shut. This time, Gabe raised a brow at him, earning a small laugh from him. 

“What, is it really that outta character for me to be good?” Jesse questioned and Gabriel rolled his eyes.

“No, but its really out of character for you to shut your mouth and not fight back on something,” Gabe gave him a leveling look, but all the sting was taken out by a smooth smirk.

“You like it when I’m bratty,” Jesse said matter-of-factly, which earned him a whack on the hip. The boy’s response was another noise followed by a light laugh. “Don’t get it. Do you want me to run my mouth or not?” He questioned with a gleeful smile. 

“How about I shut you up myself,” Gabe bit back in a voice that made Jesse shudder again. The dominant of the two was falling back into a serious roll while the slightly more submissive of the two was smiling mischievously. 

“You sure can try,” Jesse tested and gained a firmer smack to his hip. 

Gabe seemed to have a plan in mind, one that wasn’t exactly what Jesse was expecting of him. The commander leaned down, placing his legs under his boy’s legs and throwing them over his shoulder before placing a bite on his inner thigh and earning a whine. 

“Fuck, you gonna be real’ rough with me, papi?” Jesse teased, yet sounded genuinely delighted with the idea. 

Gabriel didn’t respond, continuing to litter punishing bites up and down his thighs, admiring the redness that signaled a forming bruise. It was less for Jesse and more for his own sake. It wasn’t until Jesse was squirming and murmuring out pleas for more that he stopped.

He took a moment to admire the wet spot forming on the boy’s panties, outlining his dick beautifully. Jesse reacted just as beautifully when he mouthed at his erection. He licked up and down the fabric, gently dragging his teeth over the sensitive member every so often. 

“Gabe, fuck, papi, please!” Jesse begged, trying his best to stay still for him and finding it increasingly difficult. As much as Gabe wanted to keep teasing him, he acknowledged how well behaved he was being until he had to question it and ruin it. Thus, he was feeling generous.

With a bit of maneuvering, Gabe pulled the panties aside, freeing his lover from his confines. Then, without much preamble, he took him in his mouth. Jesse’s legs jumped and tightened ever so slightly, muscles flexing as he tried to stay still. One hand flew up behind him to grip the headboard with white knuckles while the other moved to his thigh and jumped as if he was trying not to reach just the littlest bit further and pull on Gabe’s hair. 

Gabe pulled off of him a moment, taking a breath and giving him a look that made Jesse limp and compliant. “Hands on the headboard and I don’t want to see them anywhere else till I say so. Do you understand?” Jesse nodded and jerked his other hand back as if it was far too close to a snarling animal. Just as asked he held onto the headboard with both hands and sat awaiting Gabe’s next move, his chest rising and falling with each heavy breath. Once satisfied, Gabriel went back to work, sucking off his lover at a steady pace. 

“Fuck, Gabe, sir, feels so fuckin’ good. Your mouth feels so fucking good on my cock. Fuck, papi, please, fuckin’…” Gabe listened intently to every word the cowboy babbled out, his mouth running faster than his brain, as it usually did when he started really feeling it. Gabriel wasn’t satisfied with that, though, he knew he could get him passed the point of sentences and into a realm of Gabe’s name and whatever terms of endearment the cowboy could think to spout. 

In fact, it wasn’t very long at all before Jesse was falling into that wonderful, blissed out state of his. Gabe increased his effort and took him all the way to the root, causing Jesse’s back to arch off the mattress and his voice to raise an octave as the words fall into sounds. That’s when Gabe stopped, all together, removing himself from between Jesse’s thighs, even. He had no intention of letting him cum just yet. For as good as he was at the start, whether it was Gabe’s fault or not, he was still acting like a brat.

“Shit, no! Gabe, please!” He begged, hips thrusting up into thin air as if it would give him that little push he needed to get off. Gabe didn’t respond at first, pulling his panties back into place before moving up the bed and gripping Jesse’s hair. 

“Hands at your side,” he commanded, and Jesse carried the order out quickly, keeping his mouth shut for now. “You wanted me to be rough with you, right?” Gabe raised a brow and tugged on Jesse’s hair, earning a whimpering moan. 

“Y-yessir,” he stuttered out obediently. Gabe tugged him up by the hair into a sitting position, earning a high whine from him which fell into a low, guttural moan of ecstasy. 

“Say it.” 

There was no room for discussion and at this point, Jesse was back to wanting to be obedient and let Gabe have his way with him. 

“Want you to be rough with me. Want you to ruin me, fuck my face and make me beg you to fuck me. Want you to make me beg for my own release, sir,” the boy murmured, almost reverently as if he was praying. And, as everyone knows, praying is best done on your knees. 

“I want you kneeling on the floor by the foot of the bed, now,” Gabe practically growled, releasing his grip on his lover and watching him nearly trip over himself to obey his orders. Gabriel always did wonder if he disobeyed orders simply because he enjoyed being forced to do things. Then again, it was rather obvious that he was just an insufferable prick when they weren’t behind closed doors. 

Here, though, he liked to be forced into submission on most days and Gabe was more than happy to give that to him. He didn’t think he’d ever get used to seeing Jesse like this, obedient and pliant, on his knees, waiting for his next command. Gabriel didn’t make him wait long as he sat at the foot of the bed, letting his legs fall open enough for Jesse to take his place between them without even being asked. 

“If you want it, you’re gonna have to get it yourself,” Gabe teased, hand carding through his boy’s hair gently, encouragingly as a reward for his obedience. Just as asked, and almost as soon as the order left his mouth, Jesse was undoing Gabriel’s belt and zipper, fumbling a bit in his eagerness. When they first did this, Jesse was clearly embarrassed by his excited fumbling, now he knew better than to think Gabriel cared at all about it. 

It wasn’t long before Jesse had succeeded in receiving his reward, licking his lips before grimacing at the taste of lipstick that followed. He ignored it and glanced up at Gabriel, waiting for him to say when he can have his treat. In all honesty, Gabe was starting to feel just as impatient as Jesse was. 

“Go ahead, baby,” he gave a gentle tug to Jesse’s hair and with that, Jesse was licking and sucking at his cock like it was the first meal he’d had in days. Eager to please Gabe as always. He left a trail of lipstick behind, suckling along the shaft and lapping at the head before pumping his member with his hand and running his tongue along the tip and along the foreskin. 

“Come on, baby, thought you said you wanted me to fuck that pretty mouth of yours,” Gabe tried to be gentle, but he was growing rather impatient. Jesse seemed to take the hint and took his cock in his mouth, bobbing his head in a steady rhythm and letting his eyes flickering up to make eye contact with Gabriel. He took in the half-lidded look he was giving him and how well he was keeping his composure, his breathing barely picking up and his expression still holding an air of predatory hunger. 

Gabe held tightly onto Jesse’s hair, making it the only warning he’d receive before Gabe started thrusting into his mouth. He choked at first, he usually does, and at first Gabe was far too worried to enjoy it, but after a long talk, Jesse was able to convince Gabe he really did like it. The instinct never fully went away to worry about him, but now there was little more than a pause before he thrust back in.

Jesse took him beautifully after that, tilting his head back a bit and letting Gabe just use him. The moments when he’d flick his tongue across the underside or the moments that he added suction like a pulse had Gabe’s legs flexing and his toes curling into the carpet. Gabe had to give it to him, he ran his mouth off a lot, but at least he knew how to use it. 

It was beginning to be too much, though. Gabriel gave a sharp yank to Jesse’s hair, effectively signaling him to pull off, which he always did as obscenely as possible, letting spit drip from his lips and cling to Gabe’s cock as if every ounce of him wanted nothing more than to be back, wrapped around his prick. 

Jesse was panting heavily, catching his breath as best as he could. His lipstick was smeared across his chin and cheek, leaving none left on his lips as the rest was painting his lover’s length. His eyeliner was smudged from his tears and there was still a watery look in his eyes. Gabriel wanted to say he had himself under control, but he could feel just how much his resolve was slipping. 

“On the bed, naked, hands and knees,” was all Gabe had to say and Jesse was rushing to obey, finally silent like Gabe promised he’d make him. It wasn’t going to last long, though. 

Gabe took time to strip himself of the rest of his clothes, then grabbed a bottle of lube from the side table. When he turned back Jesse had his head resting against his hand as if he was still trying to catch his breath enough for what was to come. 

Gabriel couldn’t help himself from landing a smack against his lover’s ass, causing him to moan and shift so his legs were further apart for him. Gabe let out an appreciative hum as he squeezed some lube onto his fingers, rolling it between them to warm it up a bit more. He wasn’t in the mood to wait and he knew Jesse wasn’t either, so without much preamble, he inserted two fingers into his lover, knowing he could take it.

Jesse let out a breath and rocked back against his fingers invitingly. Gabriel chuckled a bit at the action. “Maybe I should just sit here and let you fuck yourself,” Gabe teased, causing Jesse to chuckle. 

“What, you getting’ tired out, old man? Thought you were supposed to be a super soldier or some shit,” Jesse teased right back, causing Gabe to laugh as well. 

“Fucking brat. I could just leave you here, you know. Make you finish sucking me off and just leave you to deal with yourself,” Gabe threatened, yet he was sure Jesse would call his bluff. 

“I’d say you wouldn’t dare -fuck-, but I know you well enough to know you’d -shit- be petty enough to prove my ass wrong,” Jesse tried to tease back, just as Gabe found his prostate. His words were closer to a desperate whimper than any sort of biting remark. Gabe added a third finger and Jesse’s body jerked as he moaned and continued to meet his thrusts with even more eagerness. “Oh, fuck, Gabe…”

“Something you want, Jess?” Gabe had it in him to tease the boy a bit more.

“Fuck…fuck me! Fucking drill me into this damn mattress and make me forget everything but your name and how good your cock feels fucking me,” he growled, baring his teeth in overwhelming pleasure as Gabe practically abused his sweet spot. Gabe felt as if he was done teasing him. He wasn’t sure either of them could wait much longer. 

He removed his finger, causing Jesse to groan and arch his back to offer himself up to Gabe even more than before. Gabriel slicked up his cock and pressed into his boy, sliding in slowly, giving him time to adjust to his size. Jesse’s hands gripped at the sheets, clawing for purchase and crying out in what was a delicious mix of pain and pleasure. 

“Oh fuck, Gabe! Yes! Shit, more!” He whined, rocking his hips back and trying to take more of him faster. Gabe let out a breath and listened, thrusting in sharply and fully sheathing his cock inside his lover, causing them both to voice their pleasure. 

“Damn, baby boy, you always feel so fucking good wrapped around my cock,” Gabe praised, placing kisses up and down his spine as he gave him time to adjust. “Take it so well for me.”

It didn’t take any time at all for Jesse to start moving his hips and whimpering out pleas of more, and Gabriel gave him just that. He started thrusting into him at a punishing pace, causing Jesse to practically scream as he slammed into him, hitting that wonderful spot with every thrust and causing Jesse’s body to jerk forward with every thrust. 

“Papi! Fuck me! Fuck ‘s good! Feels so fuckin’ good! Your cock feels so fuckin’ good!” He babbled, not even trying to hold himself back. As much as Gabe loved to hear him, he was worried that even this was too much for the soundproof walls. He grabbed him by the hair and pulled his head back, leaning down and close to his ear, barely slowing his thrusts. 

“You gotta quiet down baby. You sound so fucking pretty, but we’ll be in trouble if someone hears you, baby boy,” Gabe can see Jesse nod and try his hardest to keep his mouth shut, but at such a brutal pace, it’s hard for him to control himself. It’s not hard to realize that, even if Jesse really wanted to, he wasn’t going to be able to stay quiet. Gabriel pressed his face gently into the pillows before pulling his hand away. “Bite down, baby,” and Jesse did.

It was good enough for Gabriel as he went back to fucking into him at the same pace as before, having fallen away from it. It was delicious and yet it was far too much. Even with the extra stamina, he wasn’t going to last. 

Leaning forward, he wrapped his hand around Jesse’s cock and starting pumping him in time with his thrusts. “Come on baby, you wanna come for me?” Gabe growled as he pressed his face into the crook of his neck, biting down on instinct. Just as soon as the cowboy cries out a yes into the pillow, he’s spilling onto the sheet beneath him and crying out Gabriel’s name. 

Gabe kept at his pace, quickly spilling over as Jesse’s ass clenched and pulsed around his cock. Jesse’s moans turned to whines, his body becoming oversensitive as Gabe rode out his own climax. Taking pity on him, Gabe pulled out, watching his cum drip down his thighs with rapt attention. 

Jesse turned over onto his back and went boneless, trying to catch his breath as best as he could. His makeup was now a series of red and black smears across his face and the pillow and Gabe was vaguely aware that he was most likely going to have to throw out that pillow case, now. At the moment though, he needed to help clean Jesse up. By the time he came back with two wet washcloths, Jesse was already passed out, which wasn’t unusual. 

He cleaned up his legs with one cloth before tossing it aside and going on to trying to scrub the makeup off Jesse’s face. Apparently, he was being more abrasive than he thought, perhaps because the damn stuff wouldn’t come off. 

“Ow! Shit, calm down! Don’t sand my damn face off,” Jesse laughed and took the cloth from him, using a tablet nearby to see his reflection and try and wash it off. After a while, though he throws the cloth and set down the device, flopping back on the bed. “Don’t care how hot I look, I ain’t doing this makeup shit again,” he whined. 

“I think you just need makeup wipes,” Gabe tried, but Jesse gave him a look that said ‘Never again’ and Gabe couldn’t help but laugh. “You realize the makeup was your idea, right? Who did it anyway?” 

“Angela,” Jesse sighed, his cheeks heating up in embarrassment. 

“What’d you tell her?” Gabe looked rather amused as he laid back on the bed, discarding the ruined pillow and pulling a blanket over them both before wrapping his arms around Jesse and pulling him closer. Contrary to popular belief, Gabe could be a rather cuddly person when he felt inclined to be. 

“Told her I wanted to look pretty,” he shrugged. “She just seemed happy to do my makeup. I didn’t need to do much explaining. What’s with chicks and liking to do makeup on dudes?” He mused. 

“Not sure what women you’ve met, but I have never had that issue,” Gabe chuckled.

“You ever put makeup on?” Jesse wondered aloud and Gabe sighed out another laugh. 

“I used to wear eyeliner in high school,” he admitted, sounding completely ashamed yet amused. 

“Alright, there is no way I’m not making you wear eyeliner at some point for me,” Jesse said gleefully, a bit teasing, but mostly sounding serious. 

“Thought you just denounced makeup,” Gabe huffed, starting to feel tired and he cuddled closer to his lover and burying his head in his hair. 

“On me. Like you said, we just get makeup wipes,” Jesse tried, still sounding like he was hatching a devious plot. 

“We’ll see about that,” Gabe scoffed out a laugh. “Go to sleep, cabron.”

There was a quiet chuckle from the cowboy, then he planted a soft peck on his lover’s neck. “Love you, Gabe.”

“Love you too…even though you’re a pain in my ass.”


End file.
